An Expedient N-Terminal Attachment Methodology for the Solid Phase Peptide Synthesis

Wen-Ren Li; Sung Tsai Lin; Jian Hsiu Yang

doi:10.1055/s-2000-7947

Synlett 2000; 2000(11): 1608-1612
DOI: 10.1055/s-2000-7947

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An Expedient N-Terminal Attachment Methodology for the Solid Phase Peptide Synthesis

Wen-Ren Li^* , Sung Tsai Lin, Jian Hsiu Yang

^*Department of Chemistry, National Central University, Chung-Li, Taiwan 32054, ROC; Fax +8 86-3-4 27-79 72; E-mail: ch01@ncu.edu.tw

Abstract

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A general and successful N-terminal attachment methodology is described that allows the solid phase synthesis of oligopeptides from activated N-hydroxysuccinimide esters and amino acid lithium salts. The results of studies with different coupling systems for amide bond formation are presented. The oligomers were synthesized on solid support using a carbamate linker with final TFA/CH₂Cl₂ cleavage. This methodology was also applied for the preparation of peptide-substituted amides and esters in high purities and excellent yields.

N-hydroxysuccinimide esters - peptide-substituted amides - peptide esters - N-terminal attachment - solid-phase synthesis - amide formation

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